WO2005051954A2 - PROCEDES DE PREPARATION DE PYRAZOLO[1,5-a]-1,3,5-TRIAZINES ET LEURS INTERMEDIAIRES - Google Patents

PROCEDES DE PREPARATION DE PYRAZOLO[1,5-a]-1,3,5-TRIAZINES ET LEURS INTERMEDIAIRES Download PDF

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Publication number
WO2005051954A2
WO2005051954A2 PCT/US2004/039046 US2004039046W WO2005051954A2 WO 2005051954 A2 WO2005051954 A2 WO 2005051954A2 US 2004039046 W US2004039046 W US 2004039046W WO 2005051954 A2 WO2005051954 A2 WO 2005051954A2
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WO
WIPO (PCT)
Prior art keywords
formula
compound
contacting
methyl
carried out
Prior art date
Application number
PCT/US2004/039046
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English (en)
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WO2005051954A3 (fr
Inventor
James P. Sherbine
Shawn K. Pack
Jaan A. Pesti
Robert E. Yule
Kenneth C. Mcnulty
Original Assignee
Bristol-Myers Squibb Pharma Company
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Bristol-Myers Squibb Pharma Company filed Critical Bristol-Myers Squibb Pharma Company
Priority to BRPI0416821-6A priority Critical patent/BRPI0416821A/pt
Priority to AU2004293435A priority patent/AU2004293435A1/en
Priority to MXPA06005482A priority patent/MXPA06005482A/es
Priority to JP2006541577A priority patent/JP2007512360A/ja
Priority to CA002546652A priority patent/CA2546652A1/fr
Priority to EP04811716A priority patent/EP1706408A2/fr
Publication of WO2005051954A2 publication Critical patent/WO2005051954A2/fr
Publication of WO2005051954A3 publication Critical patent/WO2005051954A3/fr
Priority to IL175753A priority patent/IL175753A0/en
Priority to NO20062943A priority patent/NO20062943L/no

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D231/38—Nitrogen atoms
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
    • A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
    • A61P25/16—Anti-Parkinson drugs
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/22—Anxiolytics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/24—Antidepressants
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00—Drugs for disorders of the metabolism
    • A61P3/04—Anorexiants; Antiobesity agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A61P9/12—Antihypertensives
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/04—Ortho-condensed systems

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  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Veterinary Medicine (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Public Health (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Neurosurgery (AREA)
  • Biomedical Technology (AREA)
  • Neurology (AREA)
  • Cardiology (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Psychiatry (AREA)
  • Psychology (AREA)
  • Hospice & Palliative Care (AREA)
  • Pain & Pain Management (AREA)
  • Vascular Medicine (AREA)
  • Urology & Nephrology (AREA)
  • Child & Adolescent Psychology (AREA)
  • Diabetes (AREA)
  • Hematology (AREA)
  • Obesity (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Pyridine Compounds (AREA)

Abstract

La présente invention concerne de nouveaux procédés et intermédiaires de préparation d'antagonistes du récepteur de la corticolibérine (CRF) ayant la structure suivante que l'on utilise dans le traitement de troubles associés à la corticolibérine, notamment l'anxiété et la dépression.
PCT/US2004/039046 2003-11-25 2004-11-19 PROCEDES DE PREPARATION DE PYRAZOLO[1,5-a]-1,3,5-TRIAZINES ET LEURS INTERMEDIAIRES WO2005051954A2 (fr)

Priority Applications (8)

Application Number Priority Date Filing Date Title
BRPI0416821-6A BRPI0416821A (pt) 2003-11-25 2004-11-19 processo para a preparação de pirazolo[1,5-a]-1,3,5-triazinas e seus intermediários
AU2004293435A AU2004293435A1 (en) 2003-11-25 2004-11-19 Processes for the preparation of pyrazolo[1,5-a]-1,3,5-triazines and intermediates thereof
MXPA06005482A MXPA06005482A (es) 2003-11-25 2004-11-19 Procesos para la preparacion de pirazolo [1,5-a]-1,3,5-triazinas e intermediarios de los mismos.
JP2006541577A JP2007512360A (ja) 2003-11-25 2004-11-19 ピラゾロ［１，５−ａ］−１，３，５−トリアジン及びそれらの中間体の調整方法
CA002546652A CA2546652A1 (fr) 2003-11-25 2004-11-19 Procedes de preparation de pyrazolo[1,5-a]-1,3,5-triazines et leurs intermediaires
EP04811716A EP1706408A2 (fr) 2003-11-25 2004-11-19 Procedes de preparation de pyrazolo [1,5-a] -1,3,5 -triazines et leurs intermediaires
IL175753A IL175753A0 (en) 2003-11-25 2006-05-18 PROCESSES FOR THE PREPARATION OF PYRAZOLO [1,5-a]-1,3,5-TRIAZINES AND INTERMEDIATES THEREOF
NO20062943A NO20062943L (no) 2003-11-25 2006-06-23 Fremgangsmate for fremstilling av pyrazolo[1,5-alfa]-1,3,5-triaziner og intermediater derav

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
US52505003P 2003-11-25 2003-11-25
US60/525,050 2003-11-25
US10/985,236 2004-11-10
US10/985,236 US7208596B2 (en) 2003-11-25 2004-11-10 Processes for the preparation of pyrazolo[1,5-a]-1,3,5-triazines and intermediates thereof

Publications (2)

Publication Number Publication Date
WO2005051954A2 true WO2005051954A2 (fr) 2005-06-09
WO2005051954A3 WO2005051954A3 (fr) 2005-11-17

Family

ID=34636532

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US2004/039046 WO2005051954A2 (fr) 2003-11-25 2004-11-19 PROCEDES DE PREPARATION DE PYRAZOLO[1,5-a]-1,3,5-TRIAZINES ET LEURS INTERMEDIAIRES

Country Status (15)

Country Link
US (2) US7208596B2 (fr)
EP (1) EP1706408A2 (fr)
JP (1) JP2007512360A (fr)
KR (1) KR20060116208A (fr)
AR (1) AR046851A1 (fr)
AU (1) AU2004293435A1 (fr)
BR (1) BRPI0416821A (fr)
CA (1) CA2546652A1 (fr)
IL (1) IL175753A0 (fr)
MX (1) MXPA06005482A (fr)
NO (1) NO20062943L (fr)
PE (1) PE20051045A1 (fr)
RU (1) RU2006121075A (fr)
TW (1) TW200529827A (fr)
WO (1) WO2005051954A2 (fr)

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2010084050A2 (fr) 2009-01-13 2010-07-29 Novartis Ag Dérivés de quinazolinone utiles comme antagonistes vanilloïdes
EP2305652A2 (fr) 2005-12-08 2011-04-06 Novartis AG Dérivés de quinazolinone trisubstituée en tant qu'agonistes de vanilloïde
WO2011092293A2 (fr) 2010-02-01 2011-08-04 Novartis Ag Dérivés de cyclohexylamide utilisés en tant qu'antagonistes du récepteur du crf
WO2011092290A1 (fr) 2010-02-01 2011-08-04 Novartis Ag Dérivés de pyrazolo[5,1-b] utilisés en tant qu'antagonistes du récepteur de crf-1
WO2011093352A1 (fr) 2010-01-27 2011-08-04 武田薬品工業株式会社 Dérivé de thiazole
WO2011095450A1 (fr) 2010-02-02 2011-08-11 Novartis Ag Dérivés de cyclohexylamide à titre d'antagonistes du récepteur crf
WO2012164473A1 (fr) 2011-05-27 2012-12-06 Novartis Ag Dérivés de pipéridine 3-spirocyclique comme agonistes du récepteur de la ghréline
WO2013164790A1 (fr) 2012-05-03 2013-11-07 Novartis Ag Sel de l-malate de dérivés de 2,7-diaza-spiro[4.5]déc-7-yle et ses formes cristallines à titre d'agonistes des récepteurs de ghreline

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7208596B2 (en) * 2003-11-25 2007-04-24 Bristol-Myers Squibb Pharma Company Processes for the preparation of pyrazolo[1,5-a]-1,3,5-triazines and intermediates thereof

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3910907A (en) * 1973-07-09 1975-10-07 Icn Pharmaceuticals Pyrazolo(1,5-a)-1,3,5-triazines
EP0269859A2 (fr) * 1986-10-31 1988-06-08 Otsuka Pharmaceutical Co., Ltd. Composés de pyrazolotriazine
EP0594149A2 (fr) * 1992-10-20 1994-04-27 Otsuka Pharmaceutical Co., Ltd. Dérives du pyrazole condensés, méthode de préparation et inhibiteurs androgènes
US6124289A (en) * 1996-07-24 2000-09-26 Dupont Pharmaceuticals Co. Azolo triazines and pyrimidines
WO2001023388A2 (fr) * 1999-09-30 2001-04-05 Neurogen Corporation Pyrazolo[1,5,-a]-1,5-pyrimidines et pyrazolo[1,5-a]-1,3,5-triazines amino substituees
WO2002072202A1 (fr) * 2001-03-13 2002-09-19 Bristol-Myers Squibb Pharma Company 4-(2-butylamino)-2,7-dimethyl-8-(2-methyl-6-methoxypyrid-3-yl) pyrazolo-[1,5-a]-1,3,5-triazine, ses enantiomeres et sels pharmaceutiquement acceptables en tant que ligands du recepteur de la corticoliberine

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DE3722072A1 (de) * 1987-07-01 1989-01-12 Schering Ag 6,7-dihydro-pyrazolo(1,5-a)(1,3,5) triazin-2-sulfonsaeureamide, verfahren zu ihrer herstellung und ihre verwendung als mittel mit herbizider und pflanzenwuchsregulierender wirkung
JP2691317B2 (ja) * 1989-08-25 1997-12-17 株式会社大塚製薬工場 ４―ヒドロキシ―８―（３―低級アルコキシ―４―フェニルスルフィニルフェニル）ピラゾロ〔１，５―ａ〕―１，３，５―トリアジン光学活性体の塩類及びその製造方法
US5484760A (en) * 1990-12-31 1996-01-16 Monsanto Company Herbicide antidotes as safeners for reducing phytotoxicity resulting from synergistic interaction between herbicides and other pesticides
CN1088574A (zh) 1992-12-24 1994-06-29 中国科学院化学研究所 2,6-二甲基-4-叔丁基-3-硝基-苯乙氰的合成方法
US6060478A (en) * 1996-07-24 2000-05-09 Dupont Pharmaceuticals Azolo triazines and pyrimidines
US6191131B1 (en) * 1997-07-23 2001-02-20 Dupont Pharmaceuticals Company Azolo triazines and pyrimidines
RO121272B1 (ro) 1996-07-24 2007-02-28 The Du Pont Merck Pharmaceutical Company Azolotriazine şi pirimidine
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CZ68199A3 (cs) 1996-08-28 1999-11-17 Pfizer Inc. 6,5-Heterobicyklické deriváty, farmaceutická kompozice na jejich bázi a způsob léčení chorob
EP1188750B1 (fr) * 1998-12-21 2003-10-15 Lonza AG Procédé de préparation de 2,5-diamino-4,6-dihalogénopyrimidines
JP2001302658A (ja) 2000-04-18 2001-10-31 Showa Denko Kk ３−イソクロマノン類の製造方法
US7208596B2 (en) * 2003-11-25 2007-04-24 Bristol-Myers Squibb Pharma Company Processes for the preparation of pyrazolo[1,5-a]-1,3,5-triazines and intermediates thereof

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3910907A (en) * 1973-07-09 1975-10-07 Icn Pharmaceuticals Pyrazolo(1,5-a)-1,3,5-triazines
EP0269859A2 (fr) * 1986-10-31 1988-06-08 Otsuka Pharmaceutical Co., Ltd. Composés de pyrazolotriazine
EP0594149A2 (fr) * 1992-10-20 1994-04-27 Otsuka Pharmaceutical Co., Ltd. Dérives du pyrazole condensés, méthode de préparation et inhibiteurs androgènes
US6124289A (en) * 1996-07-24 2000-09-26 Dupont Pharmaceuticals Co. Azolo triazines and pyrimidines
WO2001023388A2 (fr) * 1999-09-30 2001-04-05 Neurogen Corporation Pyrazolo[1,5,-a]-1,5-pyrimidines et pyrazolo[1,5-a]-1,3,5-triazines amino substituees
WO2002072202A1 (fr) * 2001-03-13 2002-09-19 Bristol-Myers Squibb Pharma Company 4-(2-butylamino)-2,7-dimethyl-8-(2-methyl-6-methoxypyrid-3-yl) pyrazolo-[1,5-a]-1,3,5-triazine, ses enantiomeres et sels pharmaceutiquement acceptables en tant que ligands du recepteur de la corticoliberine

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* Cited by examiner, † Cited by third party
Title
BELLEC, CHRISTIAN; MAITTE, PIERRE; DESWARTE, S.: "Structure de dérivés de beta-cétonitriles. II. Tautomérie hydrazone-énehydrazine; étude des configurations." BULL. SOC. CHIM. FR., vol. 11-12, 1981, pages 441-448, XP001206873 *
DATABASE CROSSFIRE BEILSTEIN BEILSTEIN INSTITUT ZUR FOERDERUNG DER WISSENSCHAFTEN, FRANKFURT AM MAIN, DE; 1988, XP002334814 Database accession no. 3384927 (BRN) *
DATABASE CROSSFIRE BEILSTEIN BEILSTEIN INSTITUT ZUR FOERDERUNG DER WISSENSCHAFTEN, FRANKFURT AM MAIN, DE; 1988, XP002334815 Database accession no. 2981462 *
LIQI HE, PAUL J GILLIGAN, ROBERT ZACZEK, LAWRENCE W FITZGERALD, JOHN MCELROY, H-S. L. SHEN ET AL.: "4-(1,3-Dimethoxyprop-2-ylamino)-2,7-dimet hyl-8-(2,4-dichlorophenyl)-pyrazolo[1,5-a] -1,3,5-triazine: A Potent, Orally Bioavailable CRF1 Receptor Antagonist" J. MED. CHEM., vol. 43, 2000, pages 449-456, XP002325958 *
WILLY LOGEMANN, LUIGI ALMIRANTE, LORENZO CAPRIO: "Studien in der heterocyclischen Reihe, II.Mitteil.: Die Synthese von 1,3,5-Triazinen und 5-Oxy-isoxazol-Derivaten" CHEM. BER., vol. 87, 1954, page 11751179, XP009046524 *

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2305652A2 (fr) 2005-12-08 2011-04-06 Novartis AG Dérivés de quinazolinone trisubstituée en tant qu'agonistes de vanilloïde
WO2010084050A2 (fr) 2009-01-13 2010-07-29 Novartis Ag Dérivés de quinazolinone utiles comme antagonistes vanilloïdes
WO2011093352A1 (fr) 2010-01-27 2011-08-04 武田薬品工業株式会社 Dérivé de thiazole
WO2011092293A2 (fr) 2010-02-01 2011-08-04 Novartis Ag Dérivés de cyclohexylamide utilisés en tant qu'antagonistes du récepteur du crf
WO2011092290A1 (fr) 2010-02-01 2011-08-04 Novartis Ag Dérivés de pyrazolo[5,1-b] utilisés en tant qu'antagonistes du récepteur de crf-1
WO2011095450A1 (fr) 2010-02-02 2011-08-11 Novartis Ag Dérivés de cyclohexylamide à titre d'antagonistes du récepteur crf
WO2012164473A1 (fr) 2011-05-27 2012-12-06 Novartis Ag Dérivés de pipéridine 3-spirocyclique comme agonistes du récepteur de la ghréline
WO2013164790A1 (fr) 2012-05-03 2013-11-07 Novartis Ag Sel de l-malate de dérivés de 2,7-diaza-spiro[4.5]déc-7-yle et ses formes cristallines à titre d'agonistes des récepteurs de ghreline

Also Published As

Publication number Publication date
CA2546652A1 (fr) 2005-06-09
IL175753A0 (en) 2006-09-05
AR046851A1 (es) 2005-12-28
US7442792B2 (en) 2008-10-28
PE20051045A1 (es) 2005-12-29
JP2007512360A (ja) 2007-05-17
US20070161790A1 (en) 2007-07-12
MXPA06005482A (es) 2006-08-11
EP1706408A2 (fr) 2006-10-04
WO2005051954A3 (fr) 2005-11-17
AU2004293435A1 (en) 2005-06-09
TW200529827A (en) 2005-09-16
US20050143380A1 (en) 2005-06-30
US7208596B2 (en) 2007-04-24
NO20062943L (no) 2006-08-25
BRPI0416821A (pt) 2007-03-06
RU2006121075A (ru) 2008-01-10
KR20060116208A (ko) 2006-11-14

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